


Dewey gets a plaything, aka "sexual sister."

by WebbyVanderquackLover



Category: DuckTales (Cartoon 2017)
Language: English
Status: Completed
Published: 2020-09-23
Updated: 2020-09-23
Packaged: 2021-03-07 18:14:34
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,697
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26612032
Author URL: https://archiveofourown.org/users/WebbyVanderquackLover/pseuds/WebbyVanderquackLover
Summary: Dewey gets wind of Erin and Webbys sexual explorations and wants in. He gets in alright, at a cost in the very end. But, yes he does enjoy the time together.
Kudos: 2





	Dewey gets a plaything, aka "sexual sister."

**Author's Note:**

> Hope this turned out alright.

Up until now, Webby and I had been able to keep our sexploits a secret between us, Lena and Violet. However, during one of the days she and I were viewing one of our past times together, Dewey entered the room. He said he had been looking for something but I can't really remember what. It was such a surprise that both Webby and I were unsure if we had not only hidden the screen in time but also muted the volume in time. He left after he didn't find it with us. I didn't think much of it after that until a few days later he came to speak with me in private. I asked him what's up. He said he had seen the video, at least a portion of it and had later gone back to look at other ones. He had especially liked the "Master/Pet" play one and then, after doing some internet porn searches, found other sex kinks. He had clicked through most of them not really interested until he came to the "Brother/Sister" one. That one had him hooked and after watching a few videos, wanted to try it himself. The closest "sister" he knew was Webby. Hence why he was talking with me. I asked him what his point was and he openly honestly said that he was asking permission to have sex with Webby who would pretend to be his "sister" while he her "brother." 

I said I would speak to Webby about all this and get back to him later in the day. Webby was easy to find and had some time to talk so I laid out everything Dewey had said. She had to think about it and then asked me how I felt about it. I told her as long as she was ok with it and I was in the room should Dewey take it too rough and far, AND I got to masturbate as I watched, then I had no issues with it. Webby then laid out her issues. Her main fear was what if Dewey wanted to go again and told his brothers. I reassured her that Dewey would have to ask permission again and if he told his brothers, we would both deny everything he said. Her secondary was if he did take it too rough and far. I told her I'd simply kick him out of the library after I had pulled him off of her. She was fine with that so I went to find Dewey and told him everything. He agreed without a fuss even reassuring me he wouldn't "take it too far and rough." Good, I then told him to meet us in the library tonight after everyone else had gone to bed.

Webby was dressed as she usual was and promised she wouldn't let Dewey remove her pink hair bow or her cute, colorful, sexy, friendship bracelet. The fire was also lit and I had already been undressed by Webby and was sitting in the chair stroking myself slowly as I watched. Webby got into a random position she thought would "turn him on". Then Dewey entered the room and we began, particularly with Dewey pretending he had just gotten home from school.

I had just come home from school and was going up to change when I passed by the library where my sister happened to be. She's in the same grade as me and her school day starts and ends just like mine does. Before I tell you more, I should tell you about myself and my sister. My name is Dewey, I'm 12 years old, normal duckling height, nice looking (I've been told) with an average build. I'm not a sports guy but have some muscles. I get good grades and want to be a TV show host at the moment, not sure what kind of shows yet. No real girlfriend yet but I'm always looking. I've felt a few boobs but that's about all so far. Webby is my sister, she's also 12 with shoulder-length white hair, and she's also normal duckling height. She has a very nice developing figure (almost A-cups, I looked at her training bras) and my friends think she is very beautiful. She gets good grades and plays cello in the band, i think. I know she at least practices. She dates some but not steadily. I don't think she's had sex but I'm not sure.

Okay, so I was going to my room to change and passed by Webby in the Library. The door was open and she was laying on the floor on her back with one leg in a wide-open 'L' position and visible, just a little, underneath her skirt was her beautiful, colorful underwear. I see that she's sound asleep. While I'm a bit weirded out by this I'm also very turned-on by her visible underwear. I went in and stood there looking at her beautiful underwear and had an erection like I'd never had before. What am I going to do? The family could come home early. Webby was asleep in a position that she'd freak out over if anyone found her like that so I reached down and pulled the skirt over her. At least that's something. And I've had a great look.

I turned to leave and I heard, "Oh, god, what are you doing in here?" I jumped about a foot. "Sorry, Webby, I wanted to cover you up in case anyone came  
home. I-I... err..." I could see that her hand was checking her skirt as she said, "I must have... uhh... fallen asleep. Oh man. Did you....what did you... oh, shoot." "It's okay, sis, it happens to everybody, you know... happened to myself... well, not the same way... but it's okay, I underst... I'm not going to tell, if you're worried. It has happened to me too." "Oh, Dewey, I'm just so... I can't believe this...you must have seen... god, I don't believe this... I'm so..." "It's really okay. Again, it's happened to me too and I understand."

I stood there with a raging erection and couldn't wait to go do something about it when she said, "You must have had a good look, geez, I can see that you have a gigantic- you know- erection. Sorry." "Oh, I'm not, it'll give me something to remember when I have some private time. You have a beautiful body, Webby, really beautiful." "You think of me when you're getting yourself off?" "Sis, you're the prettiest girl I know and, I think, the sexiest. Now I better go before I ruin my pants. Bye." Dewey then left the room and we'd knew he'd be back. We also knew he was going to masturbate.

"Well, I jacked-off after I left the room and entered the bathroom. When I returned a short time later, nothing had changed, Webby was waiting for me as I came in. "Sorry about earlier, Dewey, I hope you understand." "Oh sure, Sis, it's weird that it's happened to us both, you know, in different bedrooms under the same roof." "Earlier, you said you think of me sometimes when you're "doing it." "Well, really, I think of you just about every time if you want the truth. I hope you don't get angry about it." "No, it's really kind of flattering. Tell you the truth, I did it last night in bed and I was thinking... uuh... of you, Dewey. So, it looks like we're even. Like you said, it can apply to this, it's kinda weird that we're both doing it but separately in different bedrooms and even thinking about each other."

"What did you think about me last night? You've never seen me undressed." Dewey said. "Oh, you know, just imagined it, what you'd be like." Webby said with a slight blush to her face. "If we did it together, you'd know what I look like. We don't have to use separate bedrooms; we could do it together." I wasn't not sure why I said that, well, I did know why, but I was surprised that I did. My sister said, "It's not like you haven't had a good eyeful already is it? More to see though, once you get me undressed.... It would be pretty sexy to do it together, help get each other off." "Wanna try it out?" Dewey said excitedly. "Well, yeah I guess we could. When?" "We've got at least a good long while before everyone gets home." "Um, well, okay, the library ok with you?" "Sure I'll get a towel, guy's get a little messy."

Webby said, "I guess this is where I get to see you naked. I'll just watch as you strip," as she sat on the floor. "I actually think it would be hotter if we undressed each other." Webby gave it some thought. "I guess you're right, plus it might make you squirm when my hand gets on your erection." So, I watched her get to work. She took off my shirts first, then my pants and stepped out of my pants with a large bulge in my briefs. Right in front of her, I watched her pull them down, stopping to free my penis when the tip got caught in the waistband. Finally, my penis flopped down pointing right at Webbys face. Her eyes got big and she said, "Oooh, you're sure excited. More of a 'big' brother, huh? You're not so 'little.'"

"So, sis, how we going to do this? Each do their own thing or? I've got a towel and some lotion." "I guess that sounds fine. You're getting me in the mood so this seems to be working. Guess it's your turn." With that I slowly reached over and took off her vest, followed by her button-down shirt. My eyes growing wide as her training bra became exposed. When I finally got her shirt off and set aside, my hands were shaking. I reached around and loosened her bra which she cupped to her developing breasts. "Ready?" she said, and dropped the training bra to the floor. "Pretty nice, aren't they?" Webby said with another blush on her face. "Oh, sis, they're beautiful; growing quite nicely if I do say so myself." They were indeed growing quite nicely. Not quite yet a-cups with cute little pointy pink nipples.

Webby just blushed then pointed to her skirt and underwear. You could see my face grow red as I knelt down to finish the job. I would not touch the friendship bracelet or hair bow per my agreement. I reached around her waist to grab the elastic waistband of her purple miniskirt then slowly pulled it down to her ankles. She stepped out of it and I set it aside reaching up to her underwear to do the same. I had to stop and admire her underwear. They were very beautiful. White all around the inside and light pink around the waistband and leg bands. They even had a cute little fake pink bown dead center of the waistband. "Are you going to get me naked or just stare at my underwear?" Webby said in a soft voice bringing me out of my stupor. I shook my head then pulled the underwear down just as slowly as I had the skirt. Once I had her underwear around her ankles, she stepped out of them. Now, I'd like to say I set the underwear aside but nope, I just had to sniff her crotch and so I did. Webby thought it was cute, blushing and giggling as I sniffed. When I was done, I set the underwear aside and she sat next to me on the floor. 

She got a dildo out of a bag she had near her and said, "Shall we begin?" I poured some lotion in my palm and began slowly stroking my penis. She scooted just a tad closer and put a pillow behind her, opened her legs, licked the dildo and started to rub the tip of the wand around her vagina lips which were now very wet. Her other hand rubbed the top of her slit slowly round and round. I moved sideways to face her and was looking right into her crotch as she slid the dildo inside. "I get to see you shoot your cum, that'll be fun." The excitement was clear in my voice. "I may cum really big with all this help, why didn't we do this a long time ago?"

It was somewhat strange to be masturbating in front of my sister but her nakedness and the fact that she was masturbating too rather brought the excitement level up; I was hard as a rock. "Oh, Dewey, I'm gonna go off. Here it... here it comes. Unghh. Unghh, OOhhh, OOOOH, AAAWWW, AAAWWW, OH I'M CUUUMMMING!!" Her face was all red and splotchy and her legs were thrust out stiffly. Clear-ish liquid shot out of her vagina and onto both herself and me. "Oh god, that was the best I've ever had. Ever," she said as she slowly stroked the dildo in and out. "Oooh, that was the best." Right about then, the tip of my penis got all tingly and I sped up my strokes and suddenly, cum began to spurt out in big arcs toward my sister. "Woooweee, Dewey, what a mess. You look like a cannon going off. Neat." I could tell Webby was really into this.

"Well, looking at you doing it gives me a lot of stimulation, my penis is still like a rock and I just finished masturbating." "I thought your penis was supposed to be limp afterwards. You sure don't look limp to me." "No, I'm really wound-up doing this with you. It's great." Webby gave some thought. "Let's do each other, then, Dewey, maybe that'll be more satisfying. Okay?" "You really don't expect me to say, 'no,' do you?" She handed me the dildo and asked, "Do you know where my clitoris is? It's very sensitive and you have to be gentle with it. Look, it's right here," and she spread the top of her vagina lips and showed me her little 'love button' peeking out at me.

"Go ahead, touch it but be gentle and get it wet first." I put a finger in my mouth and then ran it around her little button. "Oh, Oh, OOOH, that's it. Mmm."  
Wow, I had no idea that a girl could be that turned-on. I thought that all the feeling was inside. Well, live and learn. She coated her hands with lotion and began to rub me up and down as I fingered her clit and ran the dildo tip along her slit. "Put it in, Dewey, just a little and fuck me with it. Oooh, yeah, just like that. Mmmm." She was moving her hips a little as I rubbed her back and forth when she said, "In a little further, oooh, that's perfect." Her hands were gliding up and down and I was going into a blissful state. I was now fucking her with the dildo all the way in and out while I rubbed her on the outside. She was moaning and moving under my hand. "Point it up, Dewey, tip it upwards. OOOH, just like that. That's really...unggh, unngggh, UNGGH, UUUNNGGHH, oooh, oooh." As if triggered by Webbys orgasm, I suddenly spurt a burst of cum up in the air before I began to get a little exhausted.

"Oh, Webby, oh, that was great. I'm just wiped out a little." The exhaustion clear in my voice. "Well, maybe your dick will be happy for a while. We should take a short break. This was fun." "Oh, more than fun sis, fantastic. I'll dream about all of this tonight." I never thought my dreams would become reality, that I would be getting handjobs let alone anything else from my beautiful sister. I had just had two orgasms and I was quickly getting hard again. "Wow, you're getting hard again already? I guess I'll just have to keep going then. I may have a few more ideas we can try out anyways." Even though I was slightly exhausted, if my sister wants to continue because of my erection then I'm going to continue because of my erection and love for her. "What ideas sis?"

"Why don't we lie down opposite each other like this?" she said as we stretched out facing each other on our sides with my head near her knees and her head alongside my hips. I had her dildo and she raised her upper leg to open herself to me and I began to stroke across her slit gliding it in slightly between her labia as I went. Webby had the bottle of hand lotion which she squirted on her hands and began to rub all over my penis again. "Oh, god, Webby, that is sooo good. Am I doing you alright?" "Yeah, you can put it in some, that would be nice" So I slid the wand into her about half way and began to move it in, out and around. "Oh, the feeling is delicious. Rub my clit, too, okay?" Webby encouraged Dewey. "How about this?" as I moved my head toward her and begin to lick her clit area while probing her love box with the dildo. "Do it faster, faster, I'm gonna cum! Ooooh, unghhh, unghhh, unghhh, ooooh. Oh, Dewey, oh, Dewey. Mmmm. Mmmm."

She was stroking me faster and I was thrusting my hips when I suddenly went stiff and moaned as my cum spurted all over Webby. "God, I'm covered in cum. Was it good?" "Oh, Sis, it was fabulous. Best cum ever in my life thus far. You can do that to me any time you want. Any time." We just laid there opposite each other after. I was slowly licking her while she was running her tongue around the tip of my cock cleaning off the seeping cum. We laid like this for what felt like fifteen or twenty minutes with an aura of blissful feeling. It seems odd and wonderful at the same time to be hugging each other's legs and hips, but I loved it.

"God, I feel good, this has been wonderful," she said. "Oh, I never dreamed it could be this good. God, I want to fuck you. Could we do that sometime?" I asked. My question was met with silence, total silence. Neither one of us has ever done it before, it would be our first. Well, for me it would since I knew that in actuality, my "sis" had lost her virginity to her boyfriend Erin who was still watching all this sexual roleplay of mine unfold as he played with himself. Anyways, I knew she wasn't on the pill and didn't want to take any chances on getting her pregnant. "I'm not on the pill so that kills your idea. We can do other stuff though." I gave it some thought. "How about condoms?" I asked. "Hmm, I think a friend of mine might have some we can borrow, let me go ask, he's usually a night owl and won't mind me naked. He's seen me before." Webby was of course referring to Erin, who was waving a condom box in our direction, but again, neither here nor there.

I was excited all day at the idea of having my first real sex. I practically ran around the library in excitement purposely ignoring Webby getting the condoms from her boyfriend. After I heard her throat clear I asked, "Well, did you get them?" She held out a box and placed it on the table. "Well, there's a dozen. That should last us 'til tomorrow," she snickered. "I can get all of them I want, so that part is easy. Would you like to go try one?" she asked with a grin. "I thought you'd never ask" and we got back into position. My cock springing up and nearly hitting her in the face. She then leaned in and began to caress my penis with her hands. "How about a nice kiss, right here," she said as she bent down and kissed the end of my penis. "Is that nice?" she asked looking up at me. "Oh, yeah." "Well, how about this?" and she licked all around the head of my penis. I thought I'd explode, right there.

Then she said, "My turn. Please, take your time." I became a deer in the headlights staring at her developing breasts. "Like to kiss 'em, Dewey?" This brought me out of my stupor and I went to work. I took a nipple between my lips and began to pull it into my mouth. I started using a pulsing action in my  
mouth and she said, "Oooh, that's going right to my vagina. Oh, that feels really good, Dewey, really good." I was rubbing her other breast and lightly squeezing its nipple. Yes, very nice. She was rubbing my dick faster and faster and I sucked faster and faster.

After a few minutes, I realized I just had to move south. My mouth immediately followed down her stomach kissing my way to the front of her smooth, bare love triangle. "Sis, I want to kiss your pretty lips...." She blushed and I spread her legs giving her a nice, long french kiss right in the middle of her vagina. She lay back and sighed as I darted my tongue in and out. "Oh, Dewey, that's so, so good. I love you licking me there. Oooh and your tongue...." I could feel her muscles tense when I jutted my tongue in as far as I could. She had little spasms when I did that so I knew I was turning her on big time. Her knees closed against my head as I continued to lick and suck her love box. "Oh, Dewey, you've got me so hot I want to fuck right now. I can't wait. I want your cock in me right now."

I got up and got a condom out of the box, tore it open and asked Webby if she knew how it goes on. "No, but maybe there's instructions." Webby offered, hiding, per our agreement, that she knew how to put one on a guy's penis. Thankfully, there were and I was soon sheathed in a reservoir-tipped lubricated latex condom ready to slide deep into my sister's beautiful, wet love tunnel. I knelt in front of her outspread legs and pressed my penis to her waiting slit. She moved her legs as far apart as she could and I slowly lowered my penis into her pushing into her warm, moist depths. "Mmm, that's good, Dewey, really good." The feeling of Webbys vagina tightly gripping my penis was fabulous, especially when I moved in and out. She began meeting my thrusts with a circular motion of her hips that was simply delicious. What a feeling, my penis was all tingly and each stoke sent waves of ecstasy throughout my body. I was the happiest twelve-year old on earth.

I never dreamed that my sister and I would be fucking each other but having her around now that we were exploring each other's bodies was keeping my penis hard throughout all this. I had a non-stop erection for my delectable sister. Yes, delectable, she tasted wonderful. I could lick her forever but I was also finding that making love to her was as good or better. "Oh, put it in all the way, Dewey, deep. Oooo, that's great. Mmm, nice and slow" and she continued to ground her hips around as I slowly pulled in and out of her. The tension was building with every slow push and pull. She tightened her grip on my penis as she moved round and round in small circles. As I pushed in as far as I could, she whispered, "Mmm, just leave it there, don't move," and she continued to rotate her hips, moving ever so slightly back and forth. It felt like she was sucking me with her vagina. I wasn't long for this world.

"I'm gonna...cum... real... UNGHHH, UNGHHH, OH WEBBY, uuhh" and I had an orgasm so strong that it was almost painful, almost. Right then, Webby began to moan and thrust her hips to bury as much of me as possible in her love house. "Oh, Dewey, I'm cumming, too... It's sooo, uuuh, UUUH, UUUH, UNGHH, omigod, I'm... It's so... I feel... oh, you're... I want you... omigod... sooo good! Oh!" She was hugging me so tightly. I never knew she was that strong. She had her legs wrapped around my back and was squeezing me as far into her as she could with all her might. She just held me there in a bear hug of her arms and legs pressing our bodies together into one.

Slowly she relaxed her hold and let out a deep sigh. "Oh, Dewey, I never knew I could feel so wonderful. I'm just on fire, all over. Oh, I love you in me. Mmmm." I pulled out and looked down at the soggy condom drooping from the end of my dick. It really looked funny. I pulled it off and went to the john and flushed it. Back in the library, Webby said that she was a little sore. "Can I kiss it and make it better?" I offered. She laughed and said I could. So I nestled between her thighs as she swung her legs over my shoulders and began to lick her slowly. "Mmmm, nice, Dewey, nice." I've heard guys talking about giving girls oral sex and how much they just love it. Well, my sister sure does. She's moving her hips around as I poke my tongue in and out and she's letting out little moans. I move up to the top of her vagina and slip my tongue in the slit and begin to suck and play my tongue around. She's really wiggling her hips around.

"Oh, Dewey, right there, don't stop, right there. Mmmm, eeeeew." She started to buck her hips up and down jamming her vagina into my face as I kept putting my tongue in and out. Her legs went stiff, straight out and she yelled, "Oh god, don't stop, don't stop... it's so good, don't stop! OOOH, OOHH! OOHH! Uuugggggh, oh, oh, god so good!" Then, she went limp all over and I slid up and laid on top of her in a nice, post-orgasmic hug. She was still  
breathing heavily and seemed very warm under me as she hugged me tightly. She gave me a tight hug and whispered, "Oh, Dewey, that was so wonderful. I love you." We lay there for I don't know how long just enjoying the feel of our skin touching all up and down our bodies.

"Oh, Dewey, I want us to do this every day, okay?" Webby said. "I'd sure love it. I just want you as much as I can." Dewey said, a hint of lust still in his voice. So, my sister Webby and I enjoyed each other (very, very much) sexually until we both were finally too tired to do sexual things anymore. Before we went to bed, Webby reminded me that maybe sometime we could share our forbidden love with someone else special. It seemed natural for Webby to share her brother and I sure didn't object. But, that's another story. As I was about to leave the room and leave Webby for her boyfriend so they could discuss this, Erin stopped me. He was covered head to toe in his own cum. I felt his hand grab my penis and play with it a bit as he spoke to me. "You're welcome. If you want this to happen again though, I get in on the action with you and only you. We'll show your "sister" how guys make love. Fair enough?" I nodded and then went to bed a happy duckling for having played out on of my new found fantasies.


End file.
